Phenylacetylene → 1-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-one

HRID 6490

반응식

HRID 6490 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CON(C)[C:22](=[O:35])[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1>O1CCCC1>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([C:22](=[O:35])[C:18]#[C:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:24]=[C:25]([O:33][CH3:34])[C:26]=1[O:31][CH3:32]

참가 물질

5

반응물 3

HCID 10821PhenylacetyleneHCID 267535N,3,4,5-tetramethoxy-N-methyl-BenzamideHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 147633891-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-one수율 34.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and saturated aqueous sodium chloride, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo. Pour onto silica gel and elute with 20% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 0.31 g of the title compound; mp 94°-96° C.

후처리

  1. customPartition between ethyl ether and saturated aqueous sodium chloride
  2. customseparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationFilter
  5. customevaporate the solvent in vacuo
  6. additionPour onto silica gel
  7. washelute with 20% ethyl acetate/hexane
  8. customto yield a crude solid
  9. customRecrystallize (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-49f779f24ab24cde9206b27accb4fa10
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248825

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